Biosynthesis of Antimycins with a Reconstituted 3-Formamidosalicylate Pharmacophore in Escherichia coli

ACS Synthetic Biology

Volumn 4, Issue 5, 2015, Pages 559-565

  Liu, Joyce ^a,b   Zhu, Xuejun ^b   Seipke, Ryan F ^c   Zhang, Wenjun ^b  

^a University of California   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

3 formamidosalicylate; antimycin biosynthesis; formyltransferase; heterologous expression; multicomponent oxygenase; nonribosomal peptide polyketide hybrid

Indexed keywords

3 FORMAMIDOSALICYLATE; ANTIMYCIN DERIVATIVE; FORMAMIDE DERIVATIVE; NATURAL PRODUCT; NONRIBOSOMAL PEPTIDE SYNTHETASE; POLYKETIDE SYNTHASE; SALICYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ANTIMYCIN A1; BIOLOGICAL PRODUCT; CITRININ;

ANT GENE; ARTICLE; COMBINATORIAL CHEMISTRY; DRUG SYNTHESIS; ESCHERICHIA COLI; GENE; GENETIC MANIPULATION; HETEROLOGOUS EXPRESSION; HYBRID; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; REACTION ANALYSIS; STREPTOMYCES; ANALOGS AND DERIVATIVES; BACTERIAL GENE; BIOSYNTHESIS; GENETICS; METABOLISM;

ESCHERICHIA COLI; STREPTOMYCES;

ANTIMYCIN A; BIOLOGICAL PRODUCTS; ESCHERICHIA COLI; GENES, BACTERIAL; SALICYLATES; STREPTOMYCES;

EID: 84929576583     PISSN: None     EISSN: 21615063     Source Type: Journal    
DOI: 10.1021/sb5003136     Document Type: Article

References (36)

1. Dunshee, B. R., Leben, C., Keitt, G. W., and Strong, F. M. (1949) The isolation and properties of Antimycin-A J. Am. Chem. Soc. 71, 2436-2437
2. Shiomi, K., Hatae, K., Hatano, H., Matsumoto, A., Takahashi, Y., Jiang, C. L., Tomoda, H., Kobayashi, S., Tanaka, H., and Omura, S. (2005) A new antibiotic, antimycin Ag, produced by Streptomyces sp. K01-0031 J. Antibiot. 58, 74-78
3. Hosotani, N., Kumagai, K., Nakagawa, H., Shimatani, T., and Saji, I. (2005) Antimycins A10 approximately A16, seven new antimycin antibiotics produced by Streptomyces spp. SPA-10191 and SPA-8893 J. Antibiot. 58, 460-467
4. Yan, L. L., Han, N. N., Zhang, Y. Q., Yu, L. Y., Chen, J., Wei, Y. Z., Li, Q. P., Tao, L., Zheng, G. H., Yang, S. E., Jiang, C. X., Zhang, X. D., Huang, Q., Habdin, X., Hu, Q. B., Li, Z., Liu, S. W., Zhang, Z. Z., He, Q. Y., Si, S. Y., and Sun, C. H. (2010) Antimycin A18 produced by an endophytic Streptomyces albidoflavus isolated from a mangrove plant J. Antibiot. 63, 259-261
5. Han, Z., Xu, Y., McConnell, O., Liu, L., Li, Y., Qi, S., Huang, X., and Qian, P. (2012) Two antimycin A analogues from marine-derived actinomycete Streptomyces lusitanus Mar. Drugs 10, 668-676
6. Yan, Y., Chen, J., Zhang, L., Zheng, Q., Han, Y., Zhang, H., Zhang, D., Awakawa, T., Abe, I., and Liu, W. (2013) Multiplexing of combinatorial chemistry in antimycin biosynthesis: expansion of molecular diversity and utility Angew. Chem., Int. Ed. 52, 12308-12312
7. Yan, Y., Zhang, L., Ito, T., Qu, X., Asakawa, Y., Awakawa, T., Abe, I., and Liu, W. (2012) Biosynthetic pathway for high structural diversity of a common dilactone core in antimycin production Org. Lett. 14, 4142-4145
8. Hayashi, K. and Nozaki, H. (1999) Kitamycins, new antimycin antibiotics produced by Streptomyces sp J. Antibiot. 52, 325-328
9. Kozone, I., Ueda, J. Y., Takagi, M., and Shin-Ya, K. (2009) JBIR-52, a new antimycin-like compound, from Streptomyces sp. ML55 J. Antibiot. 62, 593-595
10. Vanner, S. A., Li, X., Zvanych, R., Torchia, J., Sang, J., Andrews, D. W., and Magarvey, N. A. (2013) Chemical and biosynthetic evolution of the antimycin-type depsipeptides Mol. Biosyst. 9, 2712-2719
11. Derse, P. H. and Strong, F. M. (1963) Toxicity of antimycin to fish Nature 200, 600-601
12. Wikstrom, M. K. and Berden, J. A. (1972) Oxidoreduction of cytochrome b in the presence of antimycin Biochim. Biophys. Acta 283, 403-420
13. Strangman, W. K., Kwon, H. C., Broide, D., Jensen, P. R., and Fenical, W. (2009) Potent inhibitors of pro-inflammatory cytokine production produced by a marine-derived bacterium J. Med. Chem. 52, 2317-2327
14. Schwartz, P. S., Manion, M. K., Emerson, C. B., Fry, J. S., Schulz, C. M., Sweet, I. R., and Hockenbery, D. M. (2007) 2-Methoxy antimycin reveals a unique mechanism for Bcl-x(L) inhibition Mol. Cancer Ther. 6, 2073-2080
15. Tzung, S. P., Kim, K. M., Basanez, G., Giedt, C. D., Simon, J., Zimmerberg, J., Zhang, K. Y., and Hockenbery, D. M. (2001) Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3 Nat. Cell Biol. 3, 183-191
16. Sandy, M., Rui, Z., Gallagher, J., and Zhang, W. (2012) Enzymatic synthesis of dilactone scaffold of antimycins ACS Chem. Biol. 7, 1956-1961
17. Jaitzig, J., Li, J., Sussmuth, R. D., and Neubauer, P. (2014) Reconstituted biosynthesis of the nonribosomal macrolactone antibiotic valinomycin in Escherichia coli ACS Synth. Biol. 3, 432-438
18. Boghigian, B. A. and Pfeifer, B. A. (2008) Current status, strategies, and potential for the metabolic engineering of heterologous polyketides in Escherichia coli Biotechnol. Lett. 30, 1323-1330
19. Zhang, W., Li, Y., and Tang, Y. (2008) Engineered biosynthesis of bacterial aromatic polyketides in Escherichia coli Proc. Natl. Acad. Sci. U.S.A. 105, 20683-20688
20. Schoenian, I., Paetz, C., Dickschat, J. S., Aigle, B., Leblond, P., and Spiteller, D. (2012) An unprecedented 1,2-shift in the biosynthesis of the 3-aminosalicylate moiety of antimycins ChemBioChem 13, 769-773
21. Seipke, R. F., Barke, J., Brearley, C., Hill, L., Yu, D. W., Goss, R. J., and Hutchings, M. I. (2011) A single Streptomyces symbiont makes multiple antifungals to support the fungus farming ant Acromyrmex octospinosus PLoS One 6, e22028
22. Pfeifer, B. A., Admiraal, S. J., Gramajo, H., Cane, D. E., and Khosla, C. (2001) Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli Science 291, 1790-1792
23. Seipke, R. F. and Hutchings, M. I. (2013) The regulation and biosynthesis of antimycins Beilstein J. Org. Chem. 9, 2556-2563
24. Sandy, M., Zhu, X., Rui, Z., and Zhang, W. (2013) Characterization of AntB, a promiscuous acyltransferase involved in antimycin biosynthesis Org. Lett. 15, 3396-3399
25. Kurnasov, O., Jablonski, L., Polanuyer, B., Dorrestein, P., Begley, T., and Osterman, A. (2003) Aerobic tryptophan degradation pathway in bacteria: novel kynurenine formamidase FEMS Microbiol. Lett. 227, 219-227
26. Pickens, L. B., Kim, W., Wang, P., Zhou, H., Watanabe, K., Gomi, S., and Tang, Y. (2009) Biochemical analysis of the biosynthetic pathway of an anticancer tetracycline SF2575 J. Am. Chem. Soc. 131, 17677-17689
27. Rui, Z., Petrickova, K., Skanta, F., Pospisil, S., Yang, Y., Chen, C. Y., Tsai, S. F., Floss, H. G., Petricek, M., and Yu, T. W. (2010) Biochemical and genetic insights into asukamycin biosynthesis J. Biol. Chem. 285, 24915-24924
28. Teufel, R., Mascaraque, V., Ismail, W., Voss, M., Perera, J., Eisenreich, W., Haehnel, W., and Fuchs, G. (2010) Bacterial phenylalanine and phenylacetate catabolic pathway revealed Proc. Natl. Acad. Sci. U.S.A. 107, 14390-14395
29. Grishin, A. M., Ajamian, E., Tao, L., Zhang, L., Menard, R., and Cygler, M. (2011) Structural and functional studies of the Escherichia coli phenylacetyl-CoA monooxygenase complex J. Biol. Chem. 286, 10735-10743
30. Teufel, R., Friedrich, T., and Fuchs, G. (2012) An oxygenase that forms and deoxygenates toxic epoxide Nature 483, 359-362
31. Sambrook, J. and Russell, D. W. (2001) Molecular Cloning: A Laboratory Manual, 3 rd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
32. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F., and Hopwood, D. A. (2000) Practical Streptomyces Genetics, John Innes Foundation, Norwich, U.K.
33. Pfeifer, B., Hu, Z., Licari, P., and Khosla, C. (2002) Process and metabolic strategies for improved production of Escherichia coli -derived 6-deoxyerythronolide B Appl. Environ. Microbiol. 68, 3287-3292
34. Gust, B., Challis, G. L., Fowler, K., Kieser, T., and Chater, K. F. (2003) PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin Proc. Natl. Acad. Sci. U.S.A. 100, 1541-1546
35. Seipke, R. F., Patrick, E., and Hutchings, M. I. (2014) Regulation of antimycin biosynthesis by the orphan ECF RNA polymerase sigma factor sigma (AntA.) PeerJ 2, e253
36. Hong, H. J., Hutchings, M. I., Hill, L. M., and Buttner, M. J. (2005) The role of the novel Fem protein VanK in vancomycin resistance in Streptomyces coelicolor J. Biol. Chem. 280, 13055-13061